The Minnesota Twins don’t seem to be keeping up. In fact, they resemble a grizzled, small-town sheriff reading a weekly newspaper and fighting the drug war with pencil and paper against opposition armed with drones in the air, satellite images of the countryside and encrypted cell phones.

Evidence in favor of the Twins’ front office may have evaporated with the Johan Santana trade to the Mets. No longer can this management team offer its wisdom in flipping AJ Pierzynski into three pitchers, two of whom powered the team through the better part of the 2000s. In fact, one could have traced the Chuck Knoblauch trade to the Yankees through Eric Milton, again through Carlos Silva and Nick Punto. Or explored the beauty of dumping JC Romero for Alexi Casilla, converting a 1997 draft pick into a major league infielder starting through 2012.

But none of these things matter now. All those players are no gone, some of the unceremoniously dumped, such as Casilla being cast off and returning no value following a waiver claim by the Orioles.

The worst of these historical portraits comes straight out of the childhood nightmares of every baseball fan. Johan Santana went to the Mets for Carlos Gomez, Philip Humber, Kevin Mulvey and Deolis Guerra. Gomez was flipped for JJ Hardy, who was later flipped for Brett Jacobson and Jim Hoey. Hoey was waived a year later. Jacobson remained in the system until the 2012 season. Humber became a free agent after two seasons. Mulvey went to Arizona for Jon Rauch. Rauch spent a little more than one year in the Twins bullpen. Guerra is still making his way through the system.

By contrast, the Twins sent Frank Viola to the Mets for Rick Aguilera, Kevin Tapani, David West, Tim Drummond and Jack Savage. The first two were major contributors in the 1991 World Series win. Aguilera spent ten years with the team and, in two outbound trades, fetched Frankie Rodriguez (four years of service), JJ Johnson, Kyle Lohse (five plus years) and Jason Ryan. Tapani gave six plus years and yielded four parts in an outbound trade (including Ron Coomer). In short, Frank Viola was still paying dividends in 2007, and the major parts contributed more than 25 years of major league service time.

By far worse, Minnesota’s formerly acute front office passed on other offers for Santana that might have been far superior and would have yielded distantly greater returns in terms of major league service years. The Yankees offered Phil Hughes, Melky Cabrera and one more prospect. The Red Sox offered Jacoby Ellsbury, Justin Masterson and Jed Lowrie. Ian Kennedy, supposedly untouchable for the Yanks, was traded a year later in the three-way deal that brought Curtis Granderson to New York. Anything would have been better than the Santana deal actually made. Ellsbury and Lowrie up the middle would have been years of above average big league parts.

Recent evidence suggests the situation in Minnesota is getting worse for our old-timer sheriff. John Lannan signed with the Phillies for one year at $2.5 million base and an incentive-laden deal. Meanwhile Kevin Correia accepted an offer from Minnesota for two years and $10 million total. Based on Fangraphs data, Lannan is actually the better pitcher by WAR. Ty Wigginton signed in St. Louis. Not only is Minnesota not signing players who represent good value at their budget, the front office is spending more money for the wrong players.

Possibly in the interest of planning his own obituary, our sheriff also made a terrible trade this off-season. Denard Span was sent to Washington for an exciting prospect in Alex Mayer. A proven, multi-year big league outfielder who was exactly what was most desired by the Nationals did not fetch more than one prospect. A solid prospect to be sure, but only one. Not even John Lannan before he was non-tendered, or a second-tier minor leaguer like Sammy Solis. When Billy Beane, who should from this point forward be referred to as Sir William, sent Gio Gonzalez to Capitol Hill, he got projected studs AJ Cole and Brad Peacock plus Derek Norris with Tommy Milone thrown in. Again, based on Fangraphs, Gio Gonzalez’s WAR was 3.6 for the season before the trade, Span’s was 3.9. Put simply, an every-day big league regular who is solidly above average is worth more than one prospect. Just ask the Tampa Bay Rays about Jake Odorizzi or Mike Montgomery.

What emerges from this mosaic of events in the last decade is far more unbecoming than an unfortunate choice of player(s) selected in the Santana windfall, or bad luck from one free agent signing or another. This mosaic instead could be interpreted as the clearest picture yet of a second division emerging in front office understanding of the changing game. Sadly for Twins fans, that Minnesota front office shows no sign of jumping back into the premier league.